What to check before you hit send
Open the PDF and confirm the client name, invoice number, line items, tax, and calendar due date. Click the Stripe pay-now path yourself in a private window so you catch expired Checkout sessions or a disconnected Stripe account before the client does. If the email client strips links, keep the amount due and “Pay now” wording in the body—not only inside the PDF.
Sample first-send email (workflow-shaped)
Subject: “Invoice INV-1042 for Website redesign — $2,400 due June 30.” Body: “Hi Jordan — attached is invoice INV-1042 for the website redesign milestone ($2,400, due June 30). You can review the PDF and pay by card here: [pay-now link]. Reply if the billing contact or PO needs to change.” Keep one ask, one link, one due date. Expand tone variants on the first-ask and template pages.
Step map: draft → preview → send → confirm
Draft line items and due date → preview PDF → verify Stripe pay-now opens the matching amount → send to the billing email → watch status on the invoice record → if unpaid near due, use the reminder guide. Do not skip preview: most “wrong amount” complaints start as an unchecked PDF or a stale link from a previous invoice.
Edge cases in the send workflow
Client wants ACH instead of card: still send the invoice PDF with clear remittance instructions and keep status on the same record if you track externally. Multiple stakeholders: CC AP, keep the project lead informed, but put one primary To: address. Revised invoice after a scope change: update the record and resend a new pay-now path—do not leave two live links for different totals.
Common failure modes
Wrong recipient (billing vs project contact), missing due date (“Net 30” with no calendar date), pay-now link that opens a different amount than the PDF, follow-ups that start a new thread without the invoice number, and sending before Stripe is connected. Fix those before you escalate tone. For reminder wording after send, use the invoice reminder and overdue email guides.
How this page differs from sibling guides
Use this page for the ordered send workflow. Use client payment request email for first-ask tone. Use invoice reminder email for before/after-due cadence. Use the Stripe invoice payment link page for how Checkout and invoice context fit together. Use the payment link generator to preview wording before you create a real request.